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Synthesis of transition metal complexes containing a Schiff base ligand derived from 1,10-phenanthroline-2,9-dicarboxaldehyde and 2-aminobenzenethiol

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Abstract

The synthesis of a new Schiff base containing 1,10-phenanthroline-2,9-dicarboxaldehyde and 2-aminobenzenethiol subunits is described. The reaction of 1,10-phenanthroline-2,9-dicarboxaldehyde with 2-aminobenzenethiol leads to the isolation of 2,9-bis(2-benzothiazolinyl)-1,10-phenanthroline (I) which undergoes rearrangement when reacted with cobalt, nickel, copper or zinc ions to produce complexes of the tautomeric Schiff base 2,9-bis[2-(2-mercaptophenyl)-2-azaethene]-1,10-phenanthroline (L). The [Cu(L)ClO4][ClO4] and [M(L)X2] complexes (where M = Co(II), Ni(II) and Zn(II) and X = Br) were characterized by physical and spectroscopic measurements which indicated that the ligand is acting probably as a tetradentate N4 chelating agent.

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Scheme 1
Fig. 1

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Acknowledgements

The authors express their sincere thanks to Comision de Investigación from the Universidad de Oriente for financial support as well as to Lic. Erasto Bastardo for elemental analyses.

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Correspondence to Juan R. Anacona.

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Anacona, J.R., Marquez, V.E. Synthesis of transition metal complexes containing a Schiff base ligand derived from 1,10-phenanthroline-2,9-dicarboxaldehyde and 2-aminobenzenethiol. Transition Met Chem 33, 579–583 (2008). https://doi.org/10.1007/s11243-008-9083-x

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Keywords

  • Schiff Base
  • High Spin
  • Phenanthroline
  • Schiff Base Ligand
  • Lower Energy Band